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Organic electroluminescent compound and organic electroluminescent device comprising the same

Active Publication Date: 2021-06-24
ROHM & HAAS ELECTRONICS MATERIALS KOREA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides an organic electroluminescent compound that can be used to create an organic electroluminescent device with high luminous efficiency and long lifespan properties.

Problems solved by technology

However, an OLED using these materials is problematic in deteriorating quantum efficiency and lifespan.
It is because, when an OLED is driven under high current, thermal stress occurs between an anode and a hole injection layer, and the thermal stress significantly reduces the lifespan of the device.
Further, since the organic material used in the hole transport zone has very high hole mobility, the hole-electron charge balance may be broken and quantum efficiency (cd / A) may decrease.

Method used

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  • Organic electroluminescent compound and organic electroluminescent device comprising the same
  • Organic electroluminescent compound and organic electroluminescent device comprising the same
  • Organic electroluminescent compound and organic electroluminescent device comprising the same

Examples

Experimental program
Comparison scheme
Effect test

example 2

on of Compound A-22

[0083]

[0084]1) Preparation of Compound 1-5

[0085]7.0 g of compound 1-4 (19.6 mmol), 4.0 g of 4-chlorophenylboronic acid (25.5 mmol), 1.13 g of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.98 mmol), and 6.8 g of potassium carbonate (49 mmol) were dissolved in 100 mL of tetrahydrofuran and 25 mL of distilled water in a flask, and the mixture was refluxed at 100° C. for 18 hours. After completion of the reaction, an organic layer was extracted with ethyl acetate, the remaining moisture was removed using magnesium sulfate, and the residue was dried and separated with column chromatography to obtain 6.1 g of compound 1-5 (yield: 80%)

[0086]2) Preparation of Compound A-22

[0087]6.1 g of compound 1-5 (15.7 mmol), 6.3 g of N-1,1′-biphenyl-4-yl-9,9-dimethyl-9H-fluorene-2-amine (17.3 mmol), 0.72 g of tris(dibenzylideneaceton)dipalladium(0) (0.80 mmol), 0.64 mL of tri-t-butylphosphine (1.57 mmol, 50% toluene solution), 3.0 g of sodium t-butoxide (31.4 mmol), and 160 ...

example 3

on of Compound A-13

[0088]

[0089]1) Preparation of Compound 1-7

[0090]15 g of compound 1-1 (47.2 mmol), 25 g of compound 1-6 (47.2 mmol), 2.7 g of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (2.36 mmol), and 16.3 g of potassium carbonate (118 mmol) were dissolved in 240 mL of tetrahydrofuran and 60 mL of distilled water in a flask, and the mixture was refluxed at 100° C. for 18 hours. After completion of the reaction, an organic layer was extracted with ethyl acetate, the remaining moisture was removed using magnesium sulfate, and the residue was dried and separated with column chromatography to obtain 14.8 g of compound 1-7 (yield: 49%)

[0091]2) Preparation of Compound A-13

[0092]14 g of compound 1-7 (22.1 mmol), 0.99 g of Pd(OAc)2 (4.42 mmol), 2.44 g of ligand(tricyclohexylphosphonium tetrafluoroborate) (6.63 mmol), 21.6 g of Cs2CO3 (66.3 mmol), and 110 mL of dimethyl acetamide (DMA) were stirred under reflux for 3 hours. The mixture was cooled to room temperature and distille...

example 1

Device Production of an OLED Using the Organic Electroluminescent Compound According to the Present Disclosure

[0094]An OLED using the organic electroluminescent compound according to the present disclosure was produced as follows. A transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate for an OLED (Geomatec, Japan) was subjected to an ultrasonic washing with acetone and isopropanol, sequentially, and was then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. Compound HIL-1 was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10−6 torr. Thereafter, an electric current was applied to the cell to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 90 nm on the ITO substrate. Compound HIL-2 was then introduced into another cell of said vacuu...

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Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By using the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having high luminous efficiency and / or long lifespan properties can be provided compared to conventional organic electroluminescent devices.

Description

TECHNICAL FIELD[0001]The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.BACKGROUND ART[0002]A small molecular green organic electroluminescent device (OLED) was first developed by Tang, et al., of Eastman Kodak in 1987 by using TPD / Alq3 bi-layer consisting of a light-emitting layer and a charge transport layer. Thereafter, the development of OLEDs was rapidly effected and OLEDs have been commercialized. An OLED changes electric energy into light by applying electricity to an organic light-emitting material, and commonly comprises an anode, a cathode, and an organic layer between the two electrodes. In order to enhance the efficiency and stability of an OLED, it has a multilayer structure comprising a hole transport zone, a light-emitting layer, an electron transport zone, etc.[0003]In addition, the performance of the OLED is strongly dependent on the compounds comprised in each zone or layer. Hence, a...

Claims

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Application Information

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IPC IPC(8): H01L51/00C07C211/61C09K11/06
CPCH01L51/006H01L51/5056C09K11/06C07C211/61C07D401/04C07D251/24C07D239/74C07D239/70C07D241/42C07D241/38H10K85/6572H10K85/654H10K85/623H10K50/15H10K59/10C09K2211/1029C09K2211/1044C09K2211/1059C07C211/54C07C211/60C07C2603/18C07C2603/90C09K2211/1007C09K2211/185C07D221/18C07D471/06C07D401/10C07D241/46C07D405/12H10K85/625H10K85/633H10K85/342C09K2211/1014C09K2211/1088C09K2211/1092H10K50/00C07C2603/52C09K2211/1011H10K85/626
Inventor OH, HONG-SELEE, TAE-JINYANG, JEONG-EUNLEE, YEON-GUN
Owner ROHM & HAAS ELECTRONICS MATERIALS KOREA LTD
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